EP0695365B1 - Polymerzusammensetzungen enthaltende streckmittel und ihre verwendung - Google Patents
Polymerzusammensetzungen enthaltende streckmittel und ihre verwendung Download PDFInfo
- Publication number
- EP0695365B1 EP0695365B1 EP94914236A EP94914236A EP0695365B1 EP 0695365 B1 EP0695365 B1 EP 0695365B1 EP 94914236 A EP94914236 A EP 94914236A EP 94914236 A EP94914236 A EP 94914236A EP 0695365 B1 EP0695365 B1 EP 0695365B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- matter
- analyte
- extender
- poly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/04—Enzymes or microbial cells immobilised on or in an organic carrier entrapped within the carrier, e.g. gel or hollow fibres
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/14—Enzymes or microbial cells immobilised on or in an inorganic carrier
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/807—Apparatus included in process claim, e.g. physical support structures
- Y10S436/81—Tube, bottle, or dipstick
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
- Y10T436/144444—Glucose
Definitions
- This invention relates to polymer containing compositions useful in the preparation of diagnostic and analytical devices. More particularly, it relates to compositions which alleviate a number of problems associated with the preparation of such devices.
- Dry chemistry techniques involves the production of devices which can be used to carry out sample analyses. These devices facilitate prompt and accurate measurement of particular substances. They are easy to use, thereby permitting patient self testing, "over the counter” use, and so forth.
- test strip A particularly useful form of a dry chemistry device is the test strip. While there are a vast number of test strips available, they can be described generally.
- a test strip involves a matrix which can receive a test sample.
- the matrix usually contains one or more reagents impregnated or somehow incorporated therein, which combine with the substance of interest (the "analyte") in a reaction or series of reactions leading to generation of some detectable signal, e.g., a color.
- the matrix is usually supported by some non-reactive material, such as a thermoplastic or cellulose base.
- the matrix of these test devices must be made of a material which does not deteriously effect the reaction leading to the previously mentioned detectable signal. Further, it must be sturdy and stable. These qualities are important, because test strips are usually stored for at least a short period of time before use, and deterioration of the matrix would interfere with the use of the strip in analyte determination.
- the materials used to make the matrices are preferably polymers. Examples of polymers which are used in preparing such matrices may be found in, e.g., PCT Application PCT/US91/09819, assigned to the assignee of the subject application, as well as in U.S. Patent Nos. 4,966,856 to Ito et al., 4,689,309 to Jones, and 4,868,106, to Ito et al. Some of the polymers disclosed in
- U.S. Patent Nos. 4,786,595 to Arai et al., U.S. Patent No. 4,576,793 to Koyama et al., U.S. Patent No. 4,427,632 to Okaniwa et al., U.S. Patent No. 4,258,001 to Pierce et al., U.S. Patent No. 4,147,76, to Levy et al., and U.S. Patent No. 4,060,678 to Stickler are summarized infra, and show the diverse types of polymers useful in test strip manufacture.
- An analytical element comprising a reagent layer containing a co-polymer and reactants to detect an analyte in a biological fluid, a masking layer containing TiO 2 , copolymer and Emulgen 120, and a developing layer is known from Chemical Abstracts, Vol. 100, No. 5, 1984, abstract no. 31867, p. 277.
- the three layers of the analytical element are coated successively on one side of a transparent support.
- GB-A 801 795 discloses a process for the copolymerization of a mixture of an unsaturated polyester and an unsaturated monomer, adding to said mixture a cobalt compound which inhibits surface tackiness of the resulting copolymer.
- the reagents necessary for the diagnostic reaction are incorporated, preferably via a liquid medium with the matrix polymer.
- the resulting solution, suspension, emulsion, e.g., is then poured or otherwise dispensed so as to form a thin film.
- the film is treated so as to remove the liquids present therein, and the resulting film is rolled and stored.
- appropriate lengths of film are unrolled and converted to the desired size.
- a serious problem in this procedure is that many polymer films, even when dry, exhibit a residual tackiness, stickiness, or blocking which is not surprising when one considers that many of the polymers are also used as adhesives, floor polishes, and the like.
- the coatings or films adhere to each other, and when unrolled, there is tearing or blocking and other deterioration caused because of the tackiness.
- Any approach taken to solving this problem must also consider whether the materials incorporated into the film, i.e., the reagents useful for analyte determination are damaged via the treatment.
- polymer films of the type described herein can be made in a manner which alleviates the tackiness problem without interfering with the reagents included in the film.
- a composition in the form of an aqueous emulsion was prepared, containing the following material: "UCAR 464" Emulsion Polymer 51.0 g 15% sodium dodecylbenzene sulfonate 10.0 g glucose oxidase 20 Ku peroxidase 41.4 Ku 3,3',5,5' tetra-methyl benzidine (“TMB”) 0.74 g polyvinyl pyrrolidone (“PVP”) 4.0 g Igepal CO-530 (a nonionic surfactant) 1.5 g hexanol 5.0 g 1-methoxy 2-propanol (solvent for TMB) 13.2 g
- the composition was coated onto a polycarbonate film, lightly pigmented with TiO 2 (approximately 140 m ⁇ ).
- the resulting wet film had a thickness ranging from 50-150 ⁇ m.
- the films were dried at 50°C ⁇ 20°C for 15 minutes. The films appeared to be dry and to the touch, were tack free. They were rolled for storage, as is standard for such materials. Upon unwinding, however, there was extensive damage to the coating surface due to the adhesive properties and tackiness of the coating.
- ultrafine grade mica (C4000, 8 grams) was incorporated into the composition prior to drying. All other parameters were exactly the same. The resulting films were rolled, and, upon unwinding, showed no damage whatsoever.
- extenders including 325 white wet ground mica, C-1000 micro-mica, muscovite mica, 264 mica 325 mesh, ground mica, and polymica 325.
- All types of extender yielded a composition which, when dried, produced a tack free film.
- the amount of polymer relative to the amount of mica may vary.
- a successful film can be produced with a ratio as high as 10:0.1 (polymer/mica), or as low as about 5:1.
- Example 1 The composition described in Example 1 was changed by removing the mica and using, in its stead, 8 grams of clay, i.e., "Hydrite UF", available from Georgia Kaolin Company.
- the clay has a median particle size of about 0.2 ⁇ , and a pH of anywhere from 4.2 to 5.2. It gives a residue maximum of .03% with 325-Mesh.
- the references to "residue maximum” and "325-Mesh” involve information well known in the art. To elaborate, the particles in a given sample may not be uniform, and have diameters over a range of values. Similarly, the art uses a number of screens, with openings of various size, to determine particle size of a test material.
- a screen of "325-mesh” has openings that are about 44 microns in diameter.
- a substance that leaves .03% residue when used with a 325-Mesh screen consists almost entirely of particles smaller than 44 microns in diameter.
- the resulting emulsion yielded a tack free film as did the mica containing composition. Further experiments combined both mica and clay in the same composition. The resulting films remained tack free.
- UCAR-130 Another film was prepared, using a polyvinyl acetate polymer, i.e., "UCAR-130".
- the formulation is as follows: UCAR-130 400.0 g Triton X-100 (15% solution) 26.0 g Igepal Co-530 6.0 g 1.6 M MnSO 4 (in water) 23.2 g 1.3 M NiCl 2 (in water) 23.2 g Deionized water 36.0 g Phenazine ethanesulfate .8012 g Total: 519.2 g
- This mixture produced a slurry. A portion of it (250.0 g) was then combined with a total of 18.5 g of C-4000 micromica, which is about 6.9% by weight.
- the slurry was filtered through a 100 ⁇ filter bag, and then coated and dried in the same manner as were the films of Examples 1 and 2.
- the resulting material when dried, formed a useful film, performing in the same way the films of Examples 1 and
- the nature of the extender will vary, mica and clay being especially preferred, ultrafine grades being particularly preferred.
- the amount may vary, with a weight percent of from 1-25 being preferred. A more preferred range is of from 1-10% by weight, and the optimum range being 1-3% by weight.
- Ultrafine mica is preferred, but other forms of mica, such as muscovite mica may be used.
- clays, whether treated or untreated may be used, as may clear fibrous materials, chopped to a size permitting incorporation into a film.
- the types of fibers that may be used are Orlon® , Dacron® , and ramie fibers. These fibers also serve to reinforce and strengthen the film produced.
- the percentages referred to supra for mica can also be used for these additional extenders, it being understood that more than one extender may be used, the total amount of the combination remaining within the aforementioned guidelines for good results.
- the extender can be any of the extenders used in the art, and may be used with any polymer, those polymers which can be used to make films for analytical test apparatus being especially preferred.
- Copolymers may be used in connection with the extenders, those copolymers being especially preferred containing monomers of formulas: and wherein each of R 1 , R 3 and R 4 may be hydrogen, or C1-C6 alkyl, the alkyl group in each case being optionally substituted, and R 2 is a substituted or unsubstituted aromatic moiety.
- the copolymer is a styrene/acrylic acid copolymer i.e., one where each of R 1 , R 3 and R 4 is hydrogen, and R 2 is a phenyl group.
- reagent system refers to any material or combination of materials which, upon contact with an analyte of interest, provides a detectable signal indicative of the presence and/or amount of the analyte.
- the reagent system may contain glucose oxidase, horseradish peroxidase, and 3,3',5,5'-tetramethylbenzidine. These three components constitute a standard reagent system for analysis of glucose which is well known to the field.
- Other combinations will also be known to the artisan, including, e.g., systems using cholesterol specific enzymes, such as cholesterol oxidase, non enzymatic chemistries, and so forth.
- these reagents When these reagents are incorporated into analytical films in accordance with the invention, they may be in the form of solids, such as powders, encapsulated materials, emulsions, and so forth.
- compositions of the invention are preferably formed as films. Such films are useful in test strips and similar analytical devices. These devices generally include a film of the type indicated and an inert carrier. The film and carrier may be in direct contact, or there may be intervening materials in between.
- polymers may be used in accordance with the invention. These include aqueous polymers and copolymers, and so forth. Emulsifiable polymers can also be used, as well as soluble polymers. Among the various polymers which can be used are the following:
- this can be any material which leads to generation of a signal.
- Various enzymes such as those recited in U.S. Patent No. 4,966,856 may be incorporated into the composition. Examples of these include dehydrogenase, such as glycerol dehydrogenase, oxidases, including glucose oxidase; peroxidases, including horseradish peroxidases, esterases, such as cholesterol and choline esterase, phosphatases, such as alkaline phosphatases, galactosidases, amylases, and so forth.
- the enzymes may be combined in any suitable form, such as dry powder.
- galactosides e.g, p-nitrophenyl-B-D-galactoside
- pyrogallols e.g., pyrogallols
- gallic acid 3,3',5,5'-tetramethylbenzidine other Trinder type indicators, redox indicators, and so forth
- redox indicators e.g., redox indicators, and so forth
- an extender refers to any solid material which essentially acts as a diluent in a polymeric film.
- An example of a standard extender is "china clay", a common paint extender. Mica and clay are particularly preferred extenders, as discussed supra , but chopped fibers may also be used, as well as colloidal silica. As with all extenders, ultrafine grades are preferred.
- Surfactants such as sodium dodecyl sulfonate and sodium dodecyl sulfate may also be incorporated into the compositions.
- the surfactants may act to stabilize charged indicator molecules, to enhance color formation, and/or to enhance surface contact of the sample under analysis.
- aqueous emulsion polymer and/or “aqueous polymer emulsion”, “Latex emulsion” and similar phraseology. These terms simply refer to systems where minute polymer particles are dispersed or suspended in a water matrix. When an emulsion is spread onto a support, the water evaporates and particles deform, as a result of capillary pressure. These move together, the polymer spheres frequently collapse, and the particles then stick together to yield a film. This film forming process can be enhanced by adding solvents, or by heating, so as to soften the polymers, thereby allowing sufficient deformation to form a film.
- the matrix described supra is prepared in the form of a film, cut to desired size, and then incorporated into a test strip. This incorporation may involve as little as attaching the film matrix to an inert support via, e.g., hot melt adhesives, sewing, lamination, and so forth, or via integration into a more complex system as a component thereof.
- an inert support via, e.g., hot melt adhesives, sewing, lamination, and so forth, or via integration into a more complex system as a component thereof.
- the preparation and production of such test strips is well known to the artisan, and need not be repeated here.
- test devices An alternate manner of making the test devices involves applying the matrix, in solution form, directly to the inert carrier or other support for the film.
- the composition can then be smoothed, raked, or otherwise treated to produce a smooth and uniform film upon drying.
- the resulting product can then be cut to size, and used "as is” or combined in a test device as appropriate and desired.
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (16)
- Stoffzusammensetzung, umfassend(i) eine wäßrige Polymerlösung oder wäßrige Polymeremulsion;(ii) ein Reagenziensystem für die Bestimmung eines Analyten, und(iii) eine ausreichende Menge eines Extenders, um die Klebrigkeit der Lösung oder Emulsion zu verringern.
- Stoffzusammensetzung nach Anspruch 1, wobei das Polymer ein Copolymer ist.
- Stoffzusammensetzung nach Anspruch 2, wobei das Copolymer ein Copolymer aus einem ersten Monomer der Formel und einem zweiten Monomer der Formel ist, worin R1, R3 und R4, die gleich oder verschieden sein können, Wasserstoff oder unsubstituiertes oder substitutiertes C1-C6-Alkyl sind und R2 eine substituierte oder unsubstituierte aromatische Einheit ist.
- Stoffzusammensetzung nach Anspruch 1, wobei der Extender wenigstens ein aus der Gruppe bestehend aus Glimmer und Ton ausgewählter Vertreter ist.
- Stoffzusammensetzung nach Anspruch 1, wobei das Reagenziensystem ein Enzym umfaßt, das mit dem Analyten reagiert, um ein erstes Reaktionsprodukt zu bilden, und ein Indikatormolekül, das mit dem Reaktionsprodukt oder mit einem zweiten Reaktionsprodukt reagiert, das aus der Reaktion des ersten Reaktionsprodukts und einem Reaktanten in dem Reaktionssystem gebildet wird.
- Stoffzusammensetzung nach Anspruch 5, wobei das Reagenziensystem Glucoseoxidase und Peroxidase umfaßt und der Indikator 3,3',5,5'-Tetramethylbenzidin ist.
- Stoffzusammensetzung nach Anspruch 1, des weiteren umfassend ein Tensid.
- Stoffzusammensetzung nach Anspruch 1, wobei der Extender in einer Menge im Bereich von etwa 1 bis etwa 25 Gew.-% der Zusammensetzung vorhanden ist.
- Stoffzusammensetzung nach Anspruch 8, wobei der Extender in einer Menge im Bereich von etwa 1 bis etwa 10 Gew.-% der Zusammensetzung vorhanden ist.
- Stoffzusammensetzung nach Anspruch 2, wobei das Copolymer wenigstens ein Monomer enthält, ausgewählt aus der Gruppe bestehend aus: und worin R1, R3 und R4, die gleich oder verschieden sein können, Wasserstoff oder unsubstituiertes oder substitutiertes C1-C6-Alkyl sind und R2 eine substituierte oder unsubstituierte aromatische Einheit ist.
- Stoffzusammensetzung nach Anspruch 10, wobei R1, R3 und R4 Wasserstoff sind und R2 Phenyl ist.
- Analytisches Element, das zur Bestimmung eines Analyten in einer Probe brauchbar ist, umfassend die Stoffzusammensetzung nach Anspruch 1 in Form eines Films und einen inerten Träger.
- Verfahren zur Bestimmung eines Analyten in einer Probe, umfassend das Zusammenbringen der Probe mit der Stoffzusammensetzung nach Anspruch 1 und Bestimmen der Bildung eines durch die Reaktion des Analyten mit dem Reagenziensystem gebildeten erfaßbaren Signals als Angabe für den Analyten.
- Verfahren zur Bestimmung eines Analyten in einer Probe, umfassend das Zusammenbringen der Probe mit dem analytischen Element nach Anpruch 12 und das Bestimmen der Bildung eines durch die Reaktion des Analyten mit dem Reagenziensystem gebildeten erfaßbaren Signals als Angabe für den Analyten.
- Zusammensetzung nach Anspruch 1, die auf ein Substrat aufbeschichtet ist.
- Film, umfassend eine getrocknete Zusammensetzung nach Anspruch 1.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5248593A | 1993-04-23 | 1993-04-23 | |
US52485 | 1993-04-23 | ||
PCT/US1994/004407 WO1994025622A1 (en) | 1993-04-23 | 1994-04-21 | Extender containing polymer compositions and uses thereof |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0695365A1 EP0695365A1 (de) | 1996-02-07 |
EP0695365A4 EP0695365A4 (de) | 1998-07-08 |
EP0695365B1 true EP0695365B1 (de) | 2001-08-16 |
Family
ID=21977907
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94914236A Expired - Lifetime EP0695365B1 (de) | 1993-04-23 | 1994-04-21 | Polymerzusammensetzungen enthaltende streckmittel und ihre verwendung |
Country Status (6)
Country | Link |
---|---|
US (1) | US5543299A (de) |
EP (1) | EP0695365B1 (de) |
JP (1) | JP4031029B2 (de) |
DE (1) | DE69427972T2 (de) |
ES (1) | ES2161765T3 (de) |
WO (1) | WO1994025622A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2326476A (en) * | 1997-06-17 | 1998-12-23 | Hypoguard | Reagent comprising polymeric binder, chromogen, catalyst system which initiates colour change, and sulphonate or buffer |
GB9717906D0 (en) | 1997-08-23 | 1997-10-29 | Univ Manchester | Sensor Devices And Analytical Methods |
US7955484B2 (en) * | 2005-12-14 | 2011-06-07 | Nova Biomedical Corporation | Glucose biosensor and method |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB801796A (en) * | 1955-07-09 | 1958-09-24 | Albert Ag Chem Werke | Improvements in or relating to copolymerisation |
US3916057A (en) * | 1973-08-31 | 1975-10-28 | Minnesota Mining & Mfg | Intumescent sheet material |
US3968089A (en) * | 1974-11-18 | 1976-07-06 | Jefferson Chemical Company, Inc. | Polymer-prepolymer composition prepared by polymerizing an ethylenically unsaturated monomer in the presence of an isocyanate-terminated prepolymer |
US4021384A (en) * | 1975-12-22 | 1977-05-03 | Texaco Development Corporation | Infused polymer containing polyols and polyurethane compositions based thereon |
JPS59170768A (ja) * | 1983-03-17 | 1984-09-27 | Fuji Photo Film Co Ltd | 非アイソト−プアツセイ用多層分析要素およびそれを用いるアツセイ方法 |
JPH0672883B2 (ja) * | 1985-06-19 | 1994-09-14 | コニカ株式会社 | 分析素子 |
US4689309A (en) * | 1985-09-30 | 1987-08-25 | Miles Laboratories, Inc. | Test device, method of manufacturing same and method of determining a component in a sample |
US4868106A (en) * | 1985-10-17 | 1989-09-19 | Konishiroku Photo Industry Co., Ltd. | Analytical element and method for determining a component in a test sample |
US5260195A (en) * | 1991-01-03 | 1993-11-09 | Boehringer Mannheim Corporation | Nonaqueous polymeric reagent compositions and applications thereof |
-
1994
- 1994-04-21 ES ES94914236T patent/ES2161765T3/es not_active Expired - Lifetime
- 1994-04-21 JP JP52439394A patent/JP4031029B2/ja not_active Expired - Fee Related
- 1994-04-21 EP EP94914236A patent/EP0695365B1/de not_active Expired - Lifetime
- 1994-04-21 DE DE69427972T patent/DE69427972T2/de not_active Expired - Lifetime
- 1994-04-21 WO PCT/US1994/004407 patent/WO1994025622A1/en active IP Right Grant
-
1995
- 1995-01-05 US US08/368,810 patent/US5543299A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
WO1994025622A1 (en) | 1994-11-10 |
EP0695365A4 (de) | 1998-07-08 |
JPH08509378A (ja) | 1996-10-08 |
DE69427972T2 (de) | 2002-04-04 |
JP4031029B2 (ja) | 2008-01-09 |
EP0695365A1 (de) | 1996-02-07 |
ES2161765T3 (es) | 2001-12-16 |
DE69427972D1 (de) | 2001-09-20 |
US5543299A (en) | 1996-08-06 |
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Date | Code | Title | Description |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
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17P | Request for examination filed |
Effective date: 19951113 |
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AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE ES FR GB IT |
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: USMANI, ARTHUR Inventor name: AZHAR, ABOL Inventor name: RAPKIN, MYRON Inventor name: DIEBOLD, ERIC |
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: USMANI, ARTHUR Inventor name: RAPKIN, MYRON Inventor name: DIEBOLD, ERIC |
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A4 | Supplementary search report drawn up and despatched |
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